I’ve looked at the Melbourne area and would be happy to connect offline to learn more.I go back and forth between a luxury condo (pros are easier to manage, less maintenance: cons high HOAs, limited STR rules) or a newer built home (pros are larger space, more private, higher appreciation potential: cons higher insurance, more maintenance, more upkeep, more services like lawn care/pool cleaners/etc needed).

Any red flags or recommendations when looking for a cleaner?

I’m not sure what your state requires under landlord/tenant on a “separate “ account, but it really is cleaner to keep them separate, but if you reconcile each month and show those funds there, it should be ok.

If you find a cleaner to manage it life is easy but it's also difficult to maintain because you lose them to others that can provide more consistent work.  

A great cleaner is the key.

If it does require something in person, maybe your cleaner can be paid to do it?

Because when the renter leaves and the unit is turned that shelter is done out to be cleaned or painted and the cleaners can see immediately if there is something in that shelf that needs to be tossed.Good Luck!

If you can hire a trustworthy cleaner to switch the sheets and do a quick clean then it's worth it, especially because you can charge a cleaning fee.

One location is closer to the city but the other is newer, cleaner, but further out.

If anyone out there is looking for trusted trades in HVAC, Electrical, Roofing, Foundatio, Framing, Painting, Drywall, Cleaners, Junk Removal, etc., let me know.